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However, a Classic Mac OS version of StuffIt is needed to mount the images or convert them to a newer format readable in macOS. StuffIt-compressed ShrinkWrap disk images will carry. Encrypted StuffIt archives created with the now-discontinued Private File utility will have. Newer (non-backwards compatible) Stuffit X-compressed files carry the file extension. So, StuffIt-compressed files save the resource forks of the Macintosh files inside them, and typically have the extension.

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In January 2005, JPEG compression was added as a StuffIt X compression option (see the related 'SIF Format' below).ДЇrom the mid-1990s until the 2005 acquisition by Smith Micro Software, coinciding with the release of Mac OS X v10.4 'Tiger,' StuffIt Expander came bundled with the Macintosh operating system.ДЄlthough Mac files generally did not use filename extensions, one of StuffIt's primary uses was to allow Mac files to be stored on non-Mac systems where extensions were required. It also added a 'block mode' option, error correcting 'redundancy' options to protect against data loss, and several encryption options. StuffIt X improves over the original StuffIt format and its descendants by adding multiple compression algorithms such as PPM, and BWT to LZW-type compression. It was designed to be extendable, support more compression methods, support long file names, and support Unix and Windows file attributes. With the release of OS X Public Beta, Aladdin Systems released StuffIt 6.0 which runs under OS X.ДЄlthough it was late to market, Aladdin Systems introduced the completely new StuffIt X format in September 2002 with StuffIt Deluxe 7.0 for Macintosh. Numerous programs 'wrapping' these utilities were distributed, and since these files could be opened on any machine, they were considerably more practical than StuffIt in an era when most data is cross-platform.

With the introduction of Mac OS X, newer Mac software lost their forks and no longer needed anything except the built-in Unix utilities like gzip and tar. These had little impact on the Mac market, as most of these never appeared in an easy-to-use program on the Mac.

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PC-based formats long surpassed the original StuffIt format in terms of compression, notably newer systems like RAR and 7z. The file format changed in a number of major revisions, leading to incompatible updates. Apparently as a side-effect, StuffIt once again saw few upgrades. The only ones to see any widespread use were special-purpose 'disk expanders' like DiskDoubler and SuperDisk!, which served a different niche. Several other Mac compression utilities appeared and disappeared during the 1990s, but none became a real threat to StuffIt's dominance.

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This move was a success, and Compact Pro subsequently fell out of use. Prior to this anyone attempting to use the format needed to buy StuffIt, making Compact Pro more attractive.

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ДЄ major competitive upgrade followed, accompanied by the release of the freeware StuffIt Expander, to make the format more universally readable, as well as the shareware StuffIt Lite which made it easier to produce. Because new features and techniques appeared regularly on the Macintosh platform, the shareware utility Compact Pro emerged as a competitor to StuffIt in the early 1990s. StuffIt was upgraded several times, and Lau removed himself from direct development as major upgrades to the 'internal machinery' were rare. Deluxe added a variety of additional functions, including additional compression methods and integration into the Mac Finder to allow files to be compressed from a 'Magic Menu', or seamlessly browse inside and edit compressed files without expanding them using 'True Finder Integration'.

They split the product line in two, offering StuffIt Classic in shareware and StuffIt Deluxe as a commercial package. StuffIt soon became very popular and Aladdin Systems was formed to market it (the last shareware release by Lau was version 1.5.1). By the fall of 1987 StuffIt had largely replaced PackIt in the Mac world, with many software sites even going so far as to convert existing PackIt archives to save more space. Compared to existing utilities on the Mac, notably PackIt, StuffIt offered 'one step' operation and higher compression ratios. It combined the fork-combining capabilities of utilities such as MacBinary with newer compression algorithms similar to those used in ZIP. StuffIt was originally developed in the summer of 1987 by Raymond Lau, who was then a student at Stuyvesant High School in New York City. Raymond Lau (creator), currently Smith Micro SIT!, SITD, SIT2, SIT5 (depending on file version)

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